Chris Cheatham believes forming partnerships with QBE and Guy Carpenter were the two biggest milestones in the history of his company, RiskGenius, so far. But was there ever a time when he thought it was time to pack it in and give up the idea of an InsurTech connecting commercial insurance policy wording analysis and machine learning?

“One moment when I realized we were up against something much bigger than [we planned] was back in 2015, when we had launched the beta version of RiskGenius,” he recalled. “I knew very little about insurance at the time—just what I had gleaned from being a surety attorney. We had trained algorithms on these forms that a carrier had given us and then brought in users that were different. One new user started uploading documents—literally the first user started uploading documents—and I remember looking at the first document, and our algorithms had failed on it. ‘What is this?’ I thought. It looked so much different than what we had been looking at before.”